US10212813B2 - Resin composition, prepreg, and laminated sheet - Google Patents
Resin composition, prepreg, and laminated sheet Download PDFInfo
- Publication number
- US10212813B2 US10212813B2 US13/639,351 US201113639351A US10212813B2 US 10212813 B2 US10212813 B2 US 10212813B2 US 201113639351 A US201113639351 A US 201113639351A US 10212813 B2 US10212813 B2 US 10212813B2
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- United States
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- weight
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- resin
- manufactured
- biphenyl aralkyl
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- GMCTYEAKLSFEOU-UHFFFAOYSA-N CCC1=CC=C(C2=CC=C(CC)C=C2)C=C1.OC1=CC=CC=C1.OC1=CC=CC=C1.[H]C Chemical compound CCC1=CC=C(C2=CC=C(CC)C=C2)C=C1.OC1=CC=CC=C1.OC1=CC=CC=C1.[H]C GMCTYEAKLSFEOU-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N Oc1c(cccc2)c2ccc1 Chemical compound Oc1c(cccc2)c2ccc1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- ONHQBUQZWXEPTD-UHFFFAOYSA-N CCC1=CC=C(CC)C=C1.OC1=CC=CC2=CC=CC=C12.OC1=CC=CC2=CC=CC=C12.[H]C Chemical compound CCC1=CC=C(CC)C=C1.OC1=CC=CC2=CC=CC=C12.OC1=CC=CC2=CC=CC=C12.[H]C ONHQBUQZWXEPTD-UHFFFAOYSA-N 0.000 description 1
Classifications
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/05—Insulated conductive substrates, e.g. insulated metal substrate
- H05K1/056—Insulated conductive substrates, e.g. insulated metal substrate the metal substrate being covered by an organic insulating layer
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/092—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising epoxy resins
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/098—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising condensation resins of aldehydes, e.g. with phenols, ureas or melamines
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
- B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
- B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; Imides
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09D161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
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- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
- B32B2307/3065—Flame resistant or retardant, fire resistant or retardant
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/70—Other properties
- B32B2307/726—Permeability to liquids, absorption
- B32B2307/7265—Non-permeable
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2461/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2461/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2461/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2203/20—Applications use in electrical or conductive gadgets
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- C—CHEMISTRY; METALLURGY
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31529—Next to metal
Definitions
- the present invention relates to a resin composition and more particularly relates to a resin composition for use in prepregs for printed wiring boards, a prepreg comprising the resin composition impregnated into or coated on a base material, and a laminated sheet comprising a cured product of the prepreg.
- Heat curable resins develop high heat resistance and dimensional accuracy by virtue of their crosslinked structure and thus have been expensively used in fields where high reliability is required, for example, in electronic components.
- There is an ever-increasing recent tendency toward an increase in density for example, in printed wiring boards prepared using heat curable resins.
- high adhesion to copper foils for micro wiring formation and machinability in hole making by drilling or punching are required of copper-clad laminated sheets.
- mounting by lead-free solder and imparting flame retardance without use of halogens have become required from the viewpoint of recent environmental problems, and higher heat resistance and flame retardance than those of conventional heat curable resins are required of heat curable resins for copper-clad laminated sheets.
- heat curable resin compositions that are composed of low-toxic ingredients only and do not evolve toxic gas and the like have been desired.
- Phosphorus compounds have been proposed as halogen-free flame retardants as an alternative to bromine-containing flame retardants.
- Phosphorus compounds used in flame retardation include phosphoric esters such as triphenyl phosphate and cresyl diphenyl phosphate.
- Phosphoric esters have poor resistance to alkalis and thus pose a problem that, in producing printed boards using phosphoric ester-containing epoxy resins and the like, desmear treatment or roughening process disadvantageously causes decomposition of phosphoric acid compounds, disadvantageously leading to elution of material ingredients or an increase in water absorption of the formed printed boards (patent documents 1 to 3). Further, plasticity of these phosphoric acid compounds leads to disadvantageous phenomena such as lowered glass transition points of the resins or lowered breaking strength and fracture elongation.
- Epoxy or phenolic resins with a phosphorus compound incorporated in a skeleton thereof are disadvantageous in that they are expensive and, further, a large amount of phosphorus compounds should be incorporated in the resins to provide satisfactory flame retardance, leading to a deterioration in various properties of resin compositions. Furthermore, phosphorus compounds, when burned, may disadvantageously evolve toxic compounds such as phosphine.
- Metal hydrates are known as flame retardants other than phosphorus compounds.
- aluminum hydroxide is known as a flame retardant that, when heated, causes a reaction that releases water of crystallization (patent document 5).
- the incorporation of aluminum hydroxide into resins when the amount of gibbsite that is a general structure of aluminum hydroxide is large, sometimes leads to lowered heat resistance of resins due to an influence of water of crystallization that is released upon heating.
- amino triazine skeleton-containing phenolic resins that are nitrogen-containing resins have also been proposed as other flame retardants (see patent document 6). When the amount of these resins incorporated is large, heat resistance is sometime lowered due to the evolution of decomposition gas upon heating.
- the content of the inorganic filler in the resin composition is so high that the resultant resin is hard and brittle.
- the abrasion speed of drill bits is high, and, hence, for example, the frequency of replacement of drill bits is increased due to breakage of drill bits or lowered accuracy of hole positions, that is, disadvantageously, the drilling workability is significantly lowered.
- an object of the present invention is to provide a resin composition for printed wiring boards that, while maintaining excellent flame retardance, has excellent heat resistance, reflow resistance, and drilling workability, and, at the same time, has low water absorption without use of halogen compounds and phosphorus compounds.
- a resin composition comprising:
- a prepreg comprising the above resin composition impregnated into or coated on a base material, a laminated sheet comprising a cured product of the prepreg, and a metal foil-clad laminated sheet comprising a cured product of a stack of the prepreg and a metal foil.
- the present invention can realize a resin composition for printed wiring boards that, while maintaining excellent flame retardance, has excellent heat resistance, reflow resistance, and drilling workability, and, at the same time, has low water absorption without use of halogen compounds and phosphorus compounds. Consequently, laminated sheets obtained by curing prepregs comprising the resin composition according to the present invention impregnated into or coated on base materials or metal foil-clad laminated sheets obtained by providing metal foils on the laminated sheets, despite the fact that neither halogen compounds nor phosphorus compounds are contained, have a high level of flame retardance, low water absorption, and excellent drilling workability, and are suitable as center core materials for semiconductor plastic packages where heat resistance, reflow resistance, reliability, and productivity are required.
- the resin composition according to the present invention comprises (A) a non-halogen epoxy resin, (B) a biphenyl aralkyl phenol resin, (C) a maleimide compound, and (D) an inorganic filler as indispensable ingredients. Individual ingredients constituting the resin composition according to the present invention will be described.
- non-halogen epoxy resin (A) used in the present invention examples include bisphenol A epoxy resins, bisphenol F epoxy resins, phenol novolak epoxy resins, cresol novolak epoxy resins, bisphenol A novolak epoxy resins, trifunctional phenol epoxy resins, tetrafunctional phenol epoxy resins, naphthalene epoxy resin, biphenyl epoxy resins, aralkyl novolak epoxy resins, alicyclic epoxy resins, polyol epoxy resins, compounds obtained by epoxidizing a double bond, for example, in glycidylamines, glycidyl esters, and butadiene, and compounds obtained by reacting hydroxyl-containing silicone resins with epichlorohydrin.
- non-halogen epoxy resins include bisphenol A epoxy resins, bisphenol F epoxy resins, phenol novolak epoxy resins, cresol novolak epoxy resins, bisphenol A novolak epoxy resins, trifunctional phenol epoxy resins, tetrafunctional phenol epoxy resins
- aralkyl novolak epoxy resins are preferred from the viewpoint of flame retardance.
- Such aralkyl novolak epoxy resins include phenol phenyl aralkyl epoxy resins, phenol biphenyl aralkyl epoxy resins, and naphthol aralkyl epoxy resins.
- the non-halogen epoxy resins (A) may be used solely or in a combination of two or more of them.
- the content of the non-halogen epoxy resin (A) is 20 to 60 parts by weight based on 100 parts by weight in total amount of the resins.
- the total amount of the resins refers to the total weight of the non-halogen epoxy resin (A), the biphenyl aralkyl phenol resin (B), and the maleimide compound (C).
- the biphenyl aralkyl phenol resin (B) used in the present invention is a resin represented by formula (I) that contains two or more phenolic hydroxyl groups per molecule.
- n is an integer of 1 or more.
- the content of the biphenyl aralkyl phenol resin (B) is 0.7 to 1.4 in terms of an OH/Ep ratio wherein OH represents the number of hydroxyl groups in the biphenyl aralkyl phenol resin; and Ep represents the number of epoxy groups in the non-halogen epoxy resin (A).
- OH represents the number of hydroxyl groups in the biphenyl aralkyl phenol resin
- Ep represents the number of epoxy groups in the non-halogen epoxy resin (A).
- the content of the biphenyl aralkyl phenol resin (B) is in the above-defined range in terms of the OH/Ep ratio, the heat resistance can be improved while maintaining the glass transition temperature.
- the specific content of the biphenyl aralkyl phenol resin (B) is preferably 5 to 55 parts by weight based on the total amount of the resins from the viewpoints of the glass transition temperature and heat resistance although the content of the biphenyl aralkyl phenol resin (B) may also vary depending upon the content of the non-halogen epoxy resin (A).
- the biphenyl aralkyl phenol resin (B) may be synthesized by publicly known methods.
- the weight average molecular weight of the biphenyl aralkyl phenol resin (B) is preferably about 500 to 8,000.
- the biphenyl aralkyl phenol resin (B) may be a commercially available product.
- KAYAHARD GPH-103 manufactured by Nippon Kayaku Co., Ltd. is suitable as the biphenyl aralkyl phenol resin (B).
- biphenyl aralkyl phenol resin (B) in addition to the biphenyl aralkyl phenol resin (B), other naphthol resins and/or phenolic resins may be additionally used in such an amount that does not sacrifice the effect of the present invention.
- Any compound comprising an aromatic ring, two or more of hydrogen atoms per molecule of which have been substituted by a hydroxyl group may be used as other naphthol resins and/or phenolic resins without particular limitation.
- naphthol aralkyl resins examples thereof include naphthol aralkyl resins, phenol novolak resins, alkyl phenol novolak resins, bisphenol A novolak resins, dicyclopentadiene phenol resins, xylok phenol resins, terpene-modified phenol resins, polyvinyl phenols, and aralkyl phenol resins.
- a naphthol aralkyl resin (E) represented by formula (II) is preferred from the viewpoints of heat resistance and water absorption.
- n is an integer of 1 or more.
- the amount of the naphthol aralkyl resin (E) incorporated is preferably not more than 80% by weight based on the whole amount of the phenolic resins containing the biphenyl aralkyl phenol resin (B) from the viewpoints of flame retardance, drilling workability, low water absorption, and heat resistance.
- the naphthol aralkyl resin (E) may be synthesized by a publicly known method.
- the weight average molecular weight of the naphthol aralkyl resin (E) is about 200 to 1,000.
- the naphthol aralkyl resin (E) may be a commercially available product, and, for example, SN-495 (manufactured by Nippon Steel Chemical Co., Ltd.) is suitable for use.
- any compound containing one or more maleimide groups per molecule may be used as the maleimide compound (C) without particular limitation.
- maleimide compound (C) examples thereof include N-phenylmaleimide, N-hydrophenylmaleimide, bis(4-maleimidophenyl)methane, 2,2-bis ⁇ 4-(4-maleimidophenoxy)-phenyl ⁇ propane, bis(3,5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, and bis(3,5-diethyl-4-maleimidophenyl)methane.
- the bismaleimide compounds may be in a monomer form, as well as in a prepolymer form or in the form of a prepolymer of the bismaleimide compound and an amine compound.
- These maleimide compounds (C) may be used solely or in a combination of two or more of them.
- bis(4-maleimidophenyl)methane, 2,2-bis ⁇ 4-(4-maleimidophenoxy)-phenyl ⁇ propane, and bis(3-ethyl-5-methyl-4-maleimidophenyl)methane are preferred from the viewpoint of heat resistance.
- the content of the maleimide compound (C) is preferably 5 to 50 parts by weight, more preferably 5 to 20 parts by weight, based on 100 parts by weight of the total amount of the resins from the viewpoints of heat resistance, reflow resistance, and low water absorption.
- any inorganic filler commonly used in resin compositions for electric wiring boards may be used as the inorganic filler (D) without particular limitation.
- examples thereof include silicas such as naturally occurring silica, fused silica, amorphous silica, and hollow silica, boehmite, molybdenum compounds such as molybdenum oxide and zinc molybdate, alumina, talc, calcined talc, mica, glass short fibers, and spherical glass (for example finely divided glass such as E-glass, T-glass, and D-glass).
- the inorganic fillers may be used solely or in a combination of two or more of them.
- boehmite is preferred from the viewpoints of flame retardance and heat resistance.
- the inorganic filler (D) has an average particle diameter (D50) of 0.2 to 5 ⁇ m from the viewpoint of dispersibility.
- D50 means a median diameter which is a diameter that, when a measured particle size distribution of the powder is divided into two groups, the amount of particles on a coarser side is equal to the amount of particles on a finer side.
- the D50 value of the inorganic filler is generally measured by a wet laser diffraction-scattering method.
- the content of the inorganic filler (D) is preferably 50 to 150 parts by weight, more preferably 50 to 140 parts by weight, based on 100 parts by weight of the total amount of the resins.
- the content of the inorganic filler (D) is in the above-defined range, a high level of heat resistance and a high level of moldability can be simultaneously realized.
- the inorganic filler (D) may be added solely to the resin composition, or alternatively may be added in combination with silane coupling agents or wetting/dispersing agents. Any silane coupling agent commonly used in surface treatment of inorganic materials may be used as the silane coupling agent without particular limitation.
- Examples thereof include, but are not limited to, aminosilane coupling agents such as ⁇ -aminopropyltriethoxysilane and N- ⁇ -(aminoethyl)- ⁇ -aminopropyltrimethoxysilane, epoxysilane coupling agents such as ⁇ -glycidoxypropyltrimethoxysilane, vinylsilane coupling agents such as ⁇ -methacryloxypropyltrimethoxysilane, cationic silane coupling agents such as N- ⁇ -(N-vinylbenzylaminoethyl)- ⁇ -aminopropyltrimethoxysilane hydrochloride, and phenylsilane coupling agents.
- the coupling agents may be used solely or in a combination of two or more of them.
- any dispersion stabilizer commonly used for coating materials may be used as the wetting/dispersing agent without particular limitation.
- These dispersion stabilizers may be commercially available products, and examples of suitable commercially available dispersion stabilizers include Disperbyk-110, Disperbyk-111, Disperbyk-180, Disperbyk-161, BYK-W996, BYK-W9010, and BYK-W903 manufactured by Bik-Chemie Japan K.K.
- the resin composition according to the present invention may if necessary contain a silicone powder (F).
- the silicone powder (F) functions as a flame-retarding auxiliary that retards combustion and enhances a flame retarding effect.
- the silicone powder (F) suitable for use include a finely divided product of polymethylsilsesquioxane in which siloxane bonds have been crosslinked in a three-dimensional network form, a finely divided product of an addition polymerization product of vinyl-containing dimethylpolysiloxane and methylhydrogenpolysiloxane, a product obtained by coating a surface of a finely divided product of an addition polymerization product of vinyl-containing dimethylpolysiloxane and methylhydrogenpolysiloxane with polymethylsilsesquioxane in which siloxane bonds have been crosslinked in a three-dimensional network form, and a product obtained by coating a surface of an inorganic carrier with polymethylsilsesquioxane in which siloxane
- the content of the silicone powder is preferably 1 to 30 parts by weight, more preferably 1 to 20 parts by weight, based on 100 parts by weight in total of the resins. When the content of the silicone powder exceeds 30 parts by weight, the moldability and the dispersibility are sometimes lowered.
- the resin composition according to the present invention may if necessary contain other ingredients in addition to the above ingredients.
- curing accelerators that may be contained for properly regulating the curing speed include imidazoles such as 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, tertiary amines such as 2-(dimethylaminomethyl)phenol, triethylenediamine, triethanolamine, and 1,8-diazabicyclo(5,4,0)undecene-7, organophosphines such as triphenylphosphine, diphenylphosphine, and tributylphosphine, metal compounds such as zinc octylate, and tetraphenylboron salts such as tetraphenylphosphonium tetraphenyl borate, tetraphenylphosphonium ethyltriphenyl borate, 2-ethyl-4-methyl
- the curing accelerators may be used solely or in a combination of two or more of them.
- the addition amount of the curing accelerator can be properly regulated, for example, from the viewpoints of the degree of curing of the resins and the viscosity of the resin composition and is generally about 0.01 to 15 parts by weight based on 100 parts by weight in total of the resins.
- the resin composition according to the present invention may further contain various polymer compounds such as other heat curable resins, thermoplastic resins, and oligomers and elastomers thereof, other flame retarding compounds, and additives in such an amount that does not sacrifice desired properties. They may be generally used without particular limitation as long as they are commonly used in resin compositions for printed wiring boards. Examples of flame retarding compounds include nitrogen-containing compounds such as melamine and benzoguanamine and oxazine ring-containing compounds.
- Additives include, for example, ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, antifoaming agents, dispersants, leveling agents, brighteners, and polymerization inhibitors. These additives may be used solely or in a proper combination of two or more of them according to need.
- the prepreg according to the present invention comprises the resin composition impregnated into or coated on a base material.
- base materials used in various materials for printed wiring boards may be used as the base material. Examples thereof include glass fibers such as E-glass, D-glass, S-glass, NE-glass, T-glass, and Q-glass fibers, inorganic fibers other than the glass fibers, or organic fibers such as polyimide, polyamide, and polyester fibers. These base materials may be properly selected depending upon contemplated applications and properties. Among them, E-glass fibers are more preferred from the viewpoint of an excellent balance between the coefficient of thermal expansion in a plane direction and the drilling workability.
- base materials that can be impregnated or coated with the resin composition may be used without particular limitation. Examples thereof include woven fabrics, nonwoven fabrics, rovings, chopped strand mats, and surfacing mats.
- the thickness of the base material is generally approximately 0.01 to 0.30 mm but is not limited to this thickness range.
- the prepreg according to the present invention can be produced by impregnating into or coating on the base material with the resin composition.
- the prepreg may be produced by impregnating into or coating on the base material with a resin varnish comprising the resin composition and an organic solvent and heating the impregnated or coated base material in a drier of 100 to 200° C. for 1 to 60 min to semi-cure the resin.
- the amount of the resin composition (including the inorganic filler) deposited on the base material is preferably in the range of 20 to 90% by weight based on the whole prepreg.
- the organic solvent is used to lower the viscosity of the resin composition, improve the handleability, and, at the same time, enhance impregnation of the resin composition into the glass cloth.
- Any organic solvent may be used in the resin varnish without particular limitation as long as the non-halogen epoxy resin (A), the biphenyl aralkyl phenol resin (B), and the maleimide compound (C) can be dissolved therein.
- Examples thereof include, but are not limited to, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, aromatic hydrocarbons such as benzene, toluene, and xylene, and amides such as dimethylformamide and dimethylacetamide.
- ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone
- aromatic hydrocarbons such as benzene, toluene,
- the laminated sheet according to the present invention comprises a molded (cured) product of the prepreg or a stack of a plurality of sheets of the prepreg.
- the laminated sheet is produced by providing a single sheet of the prepreg or a stack of a plurality of sheets of the prepreg, placing a metal foil of copper or aluminum provided on one surface or both surfaces of the single prepareg or the stack according to need, and subjecting the assembly to molding (curing). Any metal foil used in materials for printed wiring boards may be used without particular limitation. Techniques for conventional laminated sheets for printed wiring boards or multilayered boards may be adopted in the lamination molding.
- the lamination molding is generally carried out under conditions of the use of a multistage press, a multistage vacuum press, a continuous molding machine, an autoclave molding machine or the like, a temperature of 100 to 300° C., a pressure of 2 to 100 kgf/cm 2 , and a heating time of 0.05 to 5 hr.
- a multilayered board can be formed by lamination molding of a combination of the prepreg with a separately provided wiring board for an internal layer.
- the present invention is further illustrated by the following Examples and Comparative Examples. However, the present invention is not to be construed as being limited to them.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 50 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric, and the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a 12 ⁇ m-thick electrolytic copper foil (3EC-III, manufactured by MITSUI MINING & SMELTING CO., LTD.) was disposed on the upper surface and the lower surface of the stack, followed by lamination molding under conditions of a pressure of 30 kgf/cm 2 , a temperature of 220° C., and a time of 120 min to obtain a copper-clad laminated sheet having a 0.4 mm-thick insulating layer.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a naphthol aralkyl resin (SN-495, manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 236 g/eq.), 45 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- Kasei K.K. were dissolved in and mixed with methyl ethyl ketone. Further, a wetting/dispersing agent (BYK-W903, manufactured by Bik-Chemie Japan K.K.) (1.5 parts by weight), 120 parts by weight of boehmite (APYRAL AOH60, manufactured by Nabaltec), and 0.01 part by weight of imidazole (2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION) were mixed thereinto to obtain a varnish. The varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric, and the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (15 parts by weight), 15 parts by weight of a cresol novolak resin (PHENOLITE KA-1165, manufactured by DIC, hydroxyl equivalent: 119 g/eq.), 55 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- Kasei K.K. were dissolved in and mixed with methyl ethyl ketone. Further, 1.5 parts by weight of a wetting/dispersing agent (BYK-W903, manufactured by Bik-Chemie Japan K.K.), 120 parts by weight of boehmite (APYRAL AOH60, manufactured by Nabaltec), and 0.01 part by weight of imidazole (2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION) were mixed thereinto to obtain a varnish. The varnish was diluted with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- boehmite APIYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric, and the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (15 parts by weight), 15 parts by weight of a phenol novolak resin (TD-2090, manufactured by DIC, hydroxyl equivalent: 105 g/eq.), and 55 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (15 parts by weight), 15 parts by weight of a naphthalene skeleton phenol resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl equivalent: 153 g/eq.), and 55 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15.0 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 50 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- 20 parts by weight of a silicone rubber powder having a silicone resin-coated surface Sicone composite powder KMP-605, manufactured by The Shin-Etsu Chemical Co., Ltd.
- 0.01 part by weight of imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (40 parts by weight), 45 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- 20 parts by weight of a silicone resin powder Tospearl120, manufactured by Momentive Performance Materials Japan LLC
- 0.01 part by weight of imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (50 parts by weight), 30 parts by weight of a phenol novolak epoxy resin (EPICLON N-770, epoxy equivalent: 190 g/eq., manufactured by DIC), 5 parts by weight of a cresol novolak epoxy resin (EPICLON N-680, epoxy equivalent: 215 g/eq., manufactured by DIC), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (55 parts by weight), 15 parts by weight of a naphthalene epoxy resin (EPICLON EXA-4032-70M, epoxy equivalent: 152 g/eq., manufactured by DIC), 15 parts by weight of a naphthalene skeleton tetrafunctional epoxy resin (EPICLON EXA-4710, epoxy equivalent: 170 g/eq., manufactured by DIC), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 50 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- E-glass filler E-glass filler
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 50 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of spherical fused silica particles SC2050MOB, manufactured by Admatex
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 3 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (40 parts by weight), 55 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 5 parts by weight of a bismaleimide oligomer (DAIMIDO-100, manufactured by DAIWA KASEI KOGYO CO., LTD.) were dissolved in and mixed with methyl ethyl ketone.
- a biphenylaralkyl epoxy resin NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.
- DAIMIDO-100 bismaleimide oligomer
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 5 parts by weight of an amino triazine novolak resin (EXB-9891, hydroxyl equivalent: 137 g/eq., manufactured by DIC), 45 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 5 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), 45 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 15 parts by weight of a naphthol aralkyl resin (SN-495, manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 236 g/eq.), and 5 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), 45 parts by weight of a biphenylaralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15.0 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-eth
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (15 parts by weight), 15 parts by weight of a naphthalene skeleton phenol resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl equivalent: 153 g/eq.), 5 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), 50 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-eth
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 5 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), 45 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 5 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), 45 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- Kasei K.K. were dissolved in and mixed with methyl ethyl ketone. Further, 1.5 parts by weight of a wetting/dispersing agent (BYK-W903, manufactured by Bik-Chemie Japan K.K.), 120 parts by weight of boehmite (APYRAL AOH60, manufactured by Nabaltec), 20 parts by weight of a silicone resin powder (Tospearl120, manufactured by Momentive Performance Materials Japan LLC), 0.01 part by weight of imidazole (2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION) were mixed thereinto to obtain a varnish. The varnish was diluted with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- AOH60 boehmite
- silicone resin powder Tospearl120, manufactured by Momentive Performance Materials Japan LLC
- imidazole (2E4MZ manufactured by SHIKOKU CHEMIC
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a naphthol aralkyl resin (SN-495, manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 236 g/eq.) (35 parts by weight), 50 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a cresol novolak resin (PHENOLITE KA-1165, manufactured by DIC, hydroxyl equivalent: 119 g/eq.) (25 parts by weight), 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a phenol novolak resin (TD-2090, manufactured by DIC, hydroxyl equivalent: 105 g/eq.) (25 parts by weight), 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a naphthalene skeleton phenol resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl equivalent: 153 g/eq.) (30 parts by weight), 55 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (45 parts by weight) and 55 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a naphthol aralkyl resin (SN-495, manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 236 g/eq.), and 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a cresol novolak resin (PHENOLITE KA-1165, manufactured by DIC, hydroxyl equivalent: 119 g/eq.), and 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (15 parts by weight), 15 parts by weight of a phenol novolak resin (TD-2090, manufactured by DIC, hydroxyl equivalent: 105 g/eq.), and 70 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a naphthalene skeleton phenol resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl equivalent: 153 g/eq.), and 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (25 parts by weight), 10 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), and 65 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (14 parts by weight), 14 parts by weight of a naphthol aralkyl resin (SN-495, manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 236 g/eq.), 10 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), and 62 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (12 parts by weight), 12 parts by weight of a naphthalene skeleton phenol resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl equivalent: 153 g/eq.), 10 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), and 66 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), and 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (10 parts by weight), 10 parts by weight of a naphthol aralkyl resin (SN-495, manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 236 g/eq.), 20 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), and 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (10 parts by weight), 10 parts by weight of a naphthalene skeleton phenol resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl equivalent: 153 g/eq.), 20 parts by weight of an amino triazine novolak resin (PHENOLITE LA-3018-50P, hydroxyl equivalent: 151 g/eq., manufactured by DIC), and 60 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.) were dissolved in and mixed with methyl ethyl ketone.
- a wetting/dispersing agent BYK-W903, manufactured by Bik-Chemie Japan K.K.
- 120 parts by weight of boehmite AYRAL AOH60, manufactured by Nabaltec
- imidazole 2E4MZ, manufactured by SHIKOKU CHEMICALS CORPORATION
- the varnish was diluted with methyl ethyl ketone.
- the diluted varnish was impregnated into and coated on a 0.1 mm-thick E-glass woven fabric.
- the impregnated and coated E-glass woven fabric was heat-dried at 160° C. for 5 min to obtain a prepreg having a resin content of 47.5% by weight.
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (35 parts by weight), 50 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I. Kasei K.K.) were dissolved in and mixed with methyl ethyl ketone.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a naphthol aralkyl resin (SN-495, manufactured by Nippon Steel Chemical Co., Ltd., hydroxyl equivalent: 236 g/eq.), 45 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a cresol novolak resin (PHENOLITE KA-1165, manufactured by DIC, hydroxyl equivalent: 119 g/eq.), 45 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a biphenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a phenol novolak resin (TD-2090, manufactured by DIC, hydroxyl equivalent: 105 g/eq.), 45 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a phenyl aralkyl phenol resin (KAYAHARD GPH-103, manufactured by Nippon Kayaku Co., Ltd., hydroxyl equivalent: 231 g/eq.) (20 parts by weight), 20 parts by weight of a naphthalene skeleton phenol resin (EPICLON EXB-9500, manufactured by DIC, hydroxyl equivalent: 153 g/eq.), 45 parts by weight of a biphenyl aralkyl epoxy resin (NC-3000-FH, epoxy equivalent: 321 g/eq., manufactured by Nippon Kayaku Co., Ltd.), and 15 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (BMI-70, manufactured by K.I.
- BMI-70 bis(3-ethyl-5-methyl-4-maleimidophenyl)methane
- a copper-clad laminated sheet having a 0.4 mm-thick insulating layer was obtained in the same manner as in Example 1, except that the prepreg obtained just above was used.
- a sample that has a size of 50 ⁇ 50 mm and has been previously dried in a drier at 125° C. for 2 hr was allowed to stand under conditions of 121° C. and 2 atm for 5 hr with a pressure cooker testing apparatus (manufactured by HIRAYAMA MANUFACTURING CORPORATION), a change in weight of the sample from the weight of the sample before the standing was determined, and a percentage increase in weight of the sample from the weight before the standing was calculated as a water absorption (% by weight).
- the heat resistance, reflow resistance, and drilling workability of the metal foil-clad laminated sheets were evaluated by the following methods.
- a sample having a size of 50 ⁇ 50 mm was floated in a solder of 280° C. for 30 min, and delamination was visually inspected. The results were evaluated according to the following criteria.
- a metal foil-clad laminated sheet with a pattern having a percentage residual copper of 63% formed on both surfaces thereof was provided as an internal layer core.
- a resin sheet (ABF GX-13, thickness 37.5 ⁇ m, manufactured by Ajinomoto Fine-Techno. Co. Inc.) was stacked thereon, and a 12 ⁇ m-thick copper foil was built up on the outermost layer, followed by heating in a drier at 180° C. for 1.5 hr to prepare a four-layered board.
- the board was cut into a size of 120 ⁇ 60 mm, and reflow was performed 20 times at a highest possible temperature of 280° C. with a solder reflow apparatus (Salamander, manufactured by Shimadzu Seisakusho Ltd.), followed by visual inspection for delamination of the build-up layer.
- the results were evaluated according to the following criteria.
- the laminated sheets prepared using resin compositions according to the present invention while maintaining excellent flame retardance, have excellent heat resistance, reflow resistance, and drilling workability, and, at the same time, have low water absorption without use of halogen compounds and phosphorus compounds.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
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JP2010089801 | 2010-04-08 | ||
JP2010-89801 | 2010-04-08 | ||
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US14/580,970 Abandoned US20150111044A1 (en) | 2010-04-08 | 2014-12-23 | Resin composition, prepreg, and laminated sheet |
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US14/580,970 Abandoned US20150111044A1 (en) | 2010-04-08 | 2014-12-23 | Resin composition, prepreg, and laminated sheet |
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US (2) | US10212813B2 (ko) |
EP (1) | EP2557121B1 (ko) |
JP (2) | JP5935690B2 (ko) |
KR (2) | KR101784541B1 (ko) |
CN (3) | CN107298925B (ko) |
SG (2) | SG184504A1 (ko) |
TW (2) | TWI642719B (ko) |
WO (1) | WO2011126070A1 (ko) |
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SG10201506152WA (en) | 2010-08-31 | 2015-09-29 | Mitsubishi Gas Chemical Co | Resin composition, prepreg, and laminated sheet |
KR101507528B1 (ko) * | 2010-10-29 | 2015-03-31 | 에아.워타 가부시키가이샤 | 수지 조성물, 그것을 사용한 프리프레그 및 적층판 |
JP6115225B2 (ja) * | 2013-03-22 | 2017-04-19 | 三菱瓦斯化学株式会社 | 樹脂組成物、プリプレグ、積層板及びプリント配線板 |
JP6436378B2 (ja) * | 2014-02-06 | 2018-12-12 | 三菱瓦斯化学株式会社 | プリント配線板用樹脂組成物、プリプレグ、積層板及びプリント配線板 |
JP2015159177A (ja) * | 2014-02-24 | 2015-09-03 | 住友ベークライト株式会社 | 樹脂基板、金属張積層板、プリント配線基板、および半導体装置 |
JP6602563B2 (ja) * | 2015-06-11 | 2019-11-06 | ソマール株式会社 | 粉体塗料 |
WO2018003314A1 (ja) * | 2016-06-29 | 2018-01-04 | 三菱瓦斯化学株式会社 | 樹脂組成物、樹脂シート、多層プリント配線板及び半導体装置 |
WO2019083006A1 (ja) * | 2017-10-27 | 2019-05-02 | 積水化学工業株式会社 | 硬化性樹脂組成物、硬化物、接着剤、及び、接着フィルム |
JP6896591B2 (ja) * | 2017-11-14 | 2021-06-30 | Eneos株式会社 | プリプレグ、繊維強化複合材料及び成形体 |
US20200325292A1 (en) | 2017-12-27 | 2020-10-15 | Mitsubishi Gas Chemical Company, Inc. | Resin composition, prepreg, laminate, metal foil-clad laminate, printed wiring board, and multilayer printed wiring board |
JP7316551B2 (ja) * | 2018-08-09 | 2023-07-28 | 三菱瓦斯化学株式会社 | プリント配線板用樹脂組成物、プリプレグ、積層板、金属箔張積層板、プリント配線板及び多層プリント配線板 |
US20220025171A1 (en) * | 2018-12-12 | 2022-01-27 | Panasonic Intellectual Property Management Co., Ltd. | Resin composition, prepreg, film with resin, metal foil with resin, metal-clad laminate, and printed wiring board |
CN115551918A (zh) | 2020-05-11 | 2022-12-30 | 日铁化学材料株式会社 | 热固性树脂组合物及其固化物 |
CN114672166B (zh) * | 2020-12-24 | 2023-08-15 | 广东生益科技股份有限公司 | 一种无卤阻燃型树脂组合物及其制成的预浸料和印制电路用层压板 |
WO2023032534A1 (ja) | 2021-08-30 | 2023-03-09 | 日鉄ケミカル&マテリアル株式会社 | アリルエーテル化合物、樹脂組成物及びその硬化物 |
WO2023063282A1 (ja) * | 2021-10-15 | 2023-04-20 | 三菱瓦斯化学株式会社 | 樹脂組成物、積層体、樹脂組成物層付き半導体チップ、樹脂組成物層付き半導体チップ搭載用基板、及び半導体装置 |
WO2023063277A1 (ja) * | 2021-10-15 | 2023-04-20 | 三菱瓦斯化学株式会社 | 樹脂組成物、積層体、樹脂組成物層付き半導体チップ、樹脂組成物層付き半導体チップ搭載用基板、及び半導体装置 |
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Also Published As
Publication number | Publication date |
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CN107298925B (zh) | 2020-04-21 |
WO2011126070A1 (ja) | 2011-10-13 |
TWI658058B (zh) | 2019-05-01 |
JP6183792B2 (ja) | 2017-08-23 |
KR20170116183A (ko) | 2017-10-18 |
EP2557121A4 (en) | 2015-11-18 |
CN107298925A (zh) | 2017-10-27 |
JP2016040391A (ja) | 2016-03-24 |
JP5935690B2 (ja) | 2016-06-15 |
TWI642719B (zh) | 2018-12-01 |
KR20130045857A (ko) | 2013-05-06 |
EP2557121B1 (en) | 2020-03-04 |
TW201841971A (zh) | 2018-12-01 |
SG184504A1 (en) | 2012-11-29 |
KR101784541B1 (ko) | 2017-10-11 |
CN105400142A (zh) | 2016-03-16 |
KR101876697B1 (ko) | 2018-07-09 |
SG10201502708PA (en) | 2015-05-28 |
JPWO2011126070A1 (ja) | 2013-07-11 |
EP2557121A1 (en) | 2013-02-13 |
TW201202335A (en) | 2012-01-16 |
US20150111044A1 (en) | 2015-04-23 |
CN102947388A (zh) | 2013-02-27 |
US20130089743A1 (en) | 2013-04-11 |
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